2,3,4-Trimethoxyamphetamine

Pharmaceutical compound
TMA-3
Clinical data
Other names2,3,4-TMA; TMA-3
Routes of
administration		Oral[1]
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown[1]
Identifiers
  • 1-(2,3,4-trimethoxyphenyl)propan-2-amine
CAS Number
  • 1082-23-1
PubChem CID
  • 31012
ChemSpider
  • 28771
UNII
  • 9T3SO4A6HM
ChEMBL
  • ChEMBL30777
CompTox Dashboard (EPA)
  • DTXSID60874365
Chemical and physical data
FormulaC12H19NO3
Molar mass225.288 g·mol−1
3D model (JSmol)
  • Interactive image
  • CC(CC1=C(C(=C(C=C1)OC)OC)OC)N
  • InChI=1S/C12H19NO3/c1-8(13)7-9-5-6-10(14-2)12(16-4)11(9)15-3/h5-6,8H,7,13H2,1-4H3
  • Key:LWDQPPLPHGXYLG-UHFFFAOYSA-N

2,3,4-Trimethoxyamphetamine (2,3,4-TMA), also known as TMA-3, is a putative psychedelic drug of the phenethylamine and amphetamine families.[1][2] It is one of the possible positional isomers of trimethoxyamphetamine and is a positional isomer of 3,4,5-trimethoxyamphetamine (TMA or TMA-1).[1]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2,3,4-TMA's dose as greater than 100 mg orally and its duration as unknown.[1][2][3][4] The drug produced no effects whatsoever at a dose of 100 mg in three separate individuals.[1] Higher doses were not tested, but 2,3,4-TMA could possibly be active at higher doses.[1]

Interactions

Pharmacology

Pharmacodynamics

2,3,4-TMA shows affinity for serotonin receptors.[5][2][6][7] It substituted for DOM in rodent drug discrimination tests.[2][8]

Chemistry

Synthesis

The chemical synthesis of 2,3,4-TMA has been described.[1][2]

History

2,3,4-TMA was first described in the scientific literature by Alexander Shulgin in 1964.[2][9][10] Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1][2]

Society and culture

United States

As a positional isomer of 3,4,5-trimethoxyamphetamine (TMA), 2,3,4-TMA is a Schedule I controlled substance in the United States.[2]

See also

References

  1. ^ a b c d e f g h i Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. https://erowid.org/library/books_online/pihkal/pihkal159.shtml
  2. ^ a b c d e f g h Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
  3. ^ Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.). Hallucinogens: An Update (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91. PMID 8742795. Archived from the original on 13 July 2025.
  4. ^ Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025.
  5. ^ Glennon RA, Rosecrans JA (1982). "Indolealkylamine and phenalkylamine hallucinogens: a brief overview". Neuroscience and Biobehavioral Reviews. 6 (4): 489–497. doi:10.1016/0149-7634(82)90030-6. PMID 6757811.
  6. ^ Glennon RA, Liebowitz SM, Anderson GM (March 1980). "Serotonin receptor affinities of psychoactive phenalkylamine analogues". Journal of Medicinal Chemistry. 23 (3): 294–299. doi:10.1021/jm00177a017. PMID 7365744.
  7. ^ Glennon RA, Dukat M, Grella B, Hong S, Costantino L, Teitler M, et al. (August 2000). "Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors". Drug and Alcohol Dependence. 60 (2): 121–132. doi:10.1016/s0376-8716(99)00148-9. hdl:11380/17721. PMID 10940539.
  8. ^ Glennon RA, Young R (October 1982). "Comparison of behavioral properties of di- and tri-methoxyphenylisopropylamines". Pharmacology, Biochemistry, and Behavior. 17 (4): 603–607. doi:10.1016/0091-3057(82)90330-6. PMID 6965276.
  9. ^ Shulgin AT (July 1964). "Psychotomimetic amphetamines: methoxy 3,4-dialkoxyamphetamines". Experientia. 20 (7): 366–367. doi:10.1007/BF02147960. PMID 5855670.
  10. ^ Shulgin AT (May 1966). "The six trimethoxyphenylisopropylamines (trimethoxyamphetamines)". Journal of Medicinal Chemistry. 9 (3): 445–446. doi:10.1021/jm00321a058. PMID 5960939.
  • TMA-3 - Isomer Design
  • TMA-3 - PiHKAL - Erowid
  • TMA-3 - PiHKAL - Isomer Design
  • TMA-3 - The Shulgin Index
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